Ben Lerer spent his 20s building an email startup for 'civilized bros' — here's how he turned that into a $580 million media company

Ben Lerer founded Thrillist and is now the CEO of Group Nine, a digital holding company for four brands: The Dodo, Seeker, Thrillist, and NowThis.

Lerer comes from a family of founders. He works closely with his father, Ken, who cofounded the the Huffington Post, and his sister, Izzie, who founded animal brand The Dodo. But he has some words for people who accuse him of only being successful because he has successful parents.

Discovery recently invested $100 million in Group Nine; the company's valued at nearly $600 million.

Ben Lerer spent his 20s cofounding Thrillist, a local-recommendation site for "civilized bros," and he's now the CEO of digital holding company Group Nine.

Earlier this year he huddled with his father, Huffington Post cofounder Ken Lerer, and sister, The Dodo founder Izzie Lerer, to talk about a crazy idea they code-named "Project Family." That ultimately turned into Group Nine, a merger of four brands: Thrillist, The Dodo, video news network NowThis, and Discovery's science site, Seeker.

The process was difficult and messy.

"This is not deal making for the faint of heart," Lerer told Business Insider's podcast, "Success! How I Did It." "These companies have different boards with different investors, with different priorities. They have different management teams."

But they got it done, and Discovery invested about $100 million in the new entity.

Lerer told us how he went from a self-described "decently spoiled kid" to a digital-media mogul, and what drives him to be ambitious despite the large shadow his successful father casts.

You can listen to the full interview with him on "Success! How I Did It," here:

Subscribe to "Success! How I Did It" on Art19 or iTunes. Check out previous episodes with:

Shontell: You founded Thrillist in 2006, so that would make you an old-timer in media.

Lerer: Yup — you're an old timer too! Remember we met in 2008? So you are also very old.

Learning entrepreneurship from a young age

Ben Lerer, right, with his dad, Ken.Shontell: It's true — but you've been at this for a long time and you are from a family of founders. Your dad, Ken Lerer, cofounded the Huffington Post [now HuffPost] and was involved in all sorts of things, like BuzzFeed — even Business Insider. Your sister is a founder — she did The Dodo and she's now at Group Nine, where you are. So you guys do companies. How did that shape you growing up?

Lerer: That's shaped by my dad. For the largest portion of my childhood, he was building a corporate-communications company called Robinson Lerer Montgomery, and then went to work for AOL during the AOL-Time Warner merger. And then after that he took a little time to figure out what he wanted to do next and started HuffPo. For most of my childhood, with, like, one two- or three-year exception, he was always running his own businesses. I never, even for a second, thought about what an actual job would be for myself because I never saw the person who I looked up to having a traditional job.

Shontell: So corporate America was never on your radar? It was always, like, I'm going to start something — that's what I know how to do?

Lerer: I, admittedly, grew up like a decently spoiled kid, and so I didn't think about my future. I was a selfish little kid doing my own thing and I was a perfectly good student or whatever, but I didn't know what I wanted to be when I grew up. But I was always around media and entrepreneurship, and so that was what always interested me, but not in any particular way until obviously you graduate from college and the rubber hits the road and you're like, 'What the hell am I going to do with my life?' And that's when I first went and worked in hospitality. I worked for André Balazs straight out of school.

Shontell: And you went to Penn.

Creating Thrillist

Lerer cofounded Thrillist in 2006. Business Insider

Lerer: I went to Penn, and then came right home and moved back to New York and worked for André for a little while, and I think what I really loved about André's business was not the hospitality piece of it but the brand piece of it. And then we had this idea for Thrillist really, on the back of our own personal need, which was living in New York. And girls I knew were reading DailyCandy, and I felt like there should be something for people like me.

So a buddy from college, Adam [Rich], and I spent nights and weekends going out and eating a lot and drinking too much and checking out New York and fancied ourselves experts on fun. So that was the impetus for Thrillist, and we started it with really pathetically humble beginnings, and the media landscape evolved around us.

Shontell: So a lot to unpack there, the first of which is DailyCandy. DailyCandy, for people who might not remember, was a big email company. I think it sold for something like tens of millions of dollars.

Lerer: It sold for 125 million bucks, to Comcast.

Shontell: A ton of money. And so you want to create —

Lerer: I mean, that was like the media exit of the decade.

Shontell: Right. This is before it exits, though, you see an opportunity.

Lerer: Yeah, I mean a consumer opportunity. So what did I know about advertising or the business that DailyCandy was in? All I knew is that DailyCandy was influential with women who I knew, so they would read DailyCandy and they would do the things DailyCandy told them to do and it seemed like there was value in that. I didn't know what their business looked like, but I knew that it was clearly growing and they had been out and raising money and Bob Pittman had funded them.

Shontell: And he's now the head of I Heart Media.

Lerer: Yeah, and Bob had sort of famously founded MTV, and he's now the chairman of I Heart. But in between he built a fund called the Pilot Group, which was a private-equity fund that did some good deals and some not-as-good deals, and DailyCandy was one of the good deals, certainly. We had this idea for Thrillist, which was like a de-facto copycat of DailyCandy but with a guy's tone.

Shontell: So a newsletter for guys about how to have fun in Manhattan.

Lerer: A newsletter for guys in Manhattan. Right, exactly. And by the way, it was for a specific kind of guy. It was like Ben and Adam, age 22, 23.

Shontell: So bros.

Lerer: Real d-bags. No — I mean, yeah, bros. Civilized bros. And we ended up going to Bob. We launched Thrillist. That doesn't take a lot of money to start sending an email out to your friends, but we got a little traction, and we were right that there was an opportunity in the market. We went to Bob's fund and said, "Hey, we're doing this thing. You guys are in DailyCandy. Do you want to invest with us?"

It's fortunate he did, because actually, if you think about New York 11 years ago, there was no startup ecosystem, so nobody graduated class of 2003 Penn with me and decided to go and launch a tech company or a media company. Everyone wanted to go to Wall Street, everyone wanted to go to consulting, everyone wanted to go to business school, or everyone wanted to go to law school. That was the way.

So if Bob's fund wasn't there to give us $250,000 in the seed check, I don't know what we would have done, and I sort of had a "I'm not taking money from my dad" thing. Not that he would have given it to me, but we were, like, "Let's go raise money and do this thing and try to build it the right way." And I honestly saw it as just a learning experience. I didn't have a vision for what the future of this would look like, and we did an OK job treating every dollar like it was our last and, over what in today's startup world is an unacceptably long period of time, built a brand. It's just unbelievable how in the startup world it takes a decade to make a brand that anyone gives a sh-- about.

Finding an audience of 'civilized bros'

Thrillist found an audience through its unique brand. Ben Mueller

Shontell: Right, and so now raising money in media-land, it's a lot easier, but back then it was really tough to raise money for anyone, let alone a guy who maybe didn't have a vision, who was trying to start a newsletter company.

So what was the first iteration of Thrillist? What was that first newsletter you sent? And how did you start getting that initial traction?

Lerer: The first newsletter we sent was about a restaurant that is no longer with us, called El Rey Del Sol, which was on 14th Street. It was a Mexican restaurant that we liked, and on the fourth of May, we sent out an email telling people about what they should do on Cinco de Mayo the next day. We still read it at our company anniversary party each year because it was just so atrocious, and I mean, it's like a pleasure to read because anything is possible if that was the first piece of content we created and we built an actual company out of it.

Shontell: So who were the poor recipients of this first sad little email?

Lerer: Six hundred people, who were everyone in my contact list. And actually we were supposed to have launched several weeks prior but the day we were going to launch, we realized that we had not considered the mechanism for actually sending the email. And so I think literally we loaded it up in my Outbox and then got that kickback note that was, like, "You've sent this to too many recipients." I mean, it was as pathetic as it gets, so we hired whatever the cheapest email-newsletter-delivery thing is, and for $29 a month, which was like, "How dare they charge so much money for the service?!" And we sent out our first one.

I will say that, for whatever the quality of the content was, the one thing it had was soul. Regardless of whether it was this super-thoughtful, sophisticated whatever brand, it was a brand. It had a consistency, and it had a way of thinking about the world, and an attitude, which was, "Squeeze as much fun and enjoyment out of every day as you can." And that principle is something that even 11 years later, while the brand has been through a bunch of growth and change, it still comes back to that core proposition around, "Do the things you love better, appreciate the world around you, have fun."

Shontell: And so when did Bob come into the mix? How many of these letters were you sending before you got money to sustain yourself?

Lerer: I would guess maybe we had been creating content for somewhere between three and six months.

Shontell: And did you have traction?

Lerer: Yeah, we had traction. I think we had week over week growth that was accelerating and we had good engagement. I remember that first year where we put local businesses on the map, legitimately, where we went in and we covered something and it became one of those places where there's a line around the corner and the line doesn't stop and we got a reputation for being good at picking winners and presenting it in a light that was just different.

Shontell: So when did you start to shape your vision and realize this could actually be a real, big business?

Lerer: When DailyCandy sold was the first time we ever picked our head up. So we built for two or three years and it was getting bigger and bigger, and we always had DailyCandy's trajectory to compare it against. I remember it was, like, can you get to 35,000 subs in your first year? If you do, you're on DailyCandy trajectory. Then, can you get to 150,000 subs in year two? If you do, you're on DailyCandy trajectory.

And so we had these things that we drove toward, and then there was the same in revenue, and so we had these early DailyCandy metrics that we tracked against and tracked favorably against for two or three years, then they sold for this sort of big number. We worshipped DailyCandy and thought that they were this behemoth. But a little bit of it was "OK, well, great, we're on their trajectory, so my phone must not be working because no one's calling and offering us $125 million for the business — I don't know what's going on."

Shontell: And how many cities were you in at this point?

Lerer: I don't know: eight or 10 or 15 or six. But it felt substantive enough. The audience was great quality, but it was an email newsletter. You know, think about the reach that brands have today. Business Insider has interacted with more people since we've been sitting here than Thrillist did that year. It was hard to say, "Well, where does this thing go?" And we got this bug in our head that there was an opportunity to take this hyper-engaged consumer and find ways to monetize them outside of advertising. And we said, "What else can we do with them?" And just about this time I started investing.

Shontell: And what year is this?

Lerer: Two thousand nine.

Teaming up with his dad to find and fund startups

GettyImages

Shontell: So you are now in a bunch of markets, you've got a good subscriber base, advertisers are interested, they're working with you, but one of the rules a lot of media companies try to follow is don't just have one revenue stream. One thing that you guys figured out and that you tried was a lot of people were pairing commerce and content.

Lerer: That's that turning point for us.

Shontell: Right: So you found this company, JackThreads, and they were a clothing company and you bought them.

Lerer: And this was because I was investing. Is it worth giving that backstory? The LHV backstory? So my dad is running HuffPo, or he's the chairman of HuffPo, and I'm building Thrillist and — actually this comes back to BI — Henry Blodget, my dad's friend, calls him and says, "I'm starting this thing and I'm raising a little bit of money," and so my dad says, "Hey, my friend Henry's starting this thing — what do you think?" He sort of, like, asks my opinion, but like certainly not asking me for any money, because I don't have any, and we're, like, OK sure. So we give Henry a little bit of money and then we make eight or 10 investments in a year or so, and then they start to do well. Just like BI, they're all starting to gain a little momentum. One of them is —

Shontell: BuzzFeed.

Lerer: BuzzFeed — smart, yes, one of them is BuzzFeed.

Shontell: I know your portfolio better than you do.

Lerer: Right, yup. My dad one day comes to me and goes, "Hey, you know what, I'm an old dude. I've been around a little bit; it's really interesting what's happening right now. Your friends want to go and do tech startups suddenly. I feel like something is happening here and we should try to get involved."

And I said: "Yeah, I appreciate that point. I have a job, you have a job, and I don't even know what you're talking about." And he said, "We should raise a fund and do some investing."

And I said, "That's actually not a terrible idea." The real impetus for it was he read the funding story about Foursquare and he's, like, "I wish we had invested in that." And I'm, like, "I know those dudes. We could have invested in that."

And that was when he said: "You know all the kids are starting companies, and I bet I could raise a little bit of money for us from my friends. Let's put these things together and see if we can start a little fund." And so we raised an $8.5 million fund.

Shontell: And this is Lerer Ventures.

Lerer: And so we started investing and that was an amazing vintage of New York companies. The first generation of great New York tech companies. Then, when my dad sold HuffPo, he said, "Well, what am I going to do now?" And this LV thing is really working and we said, "Let's make this a little more serious," and so then we went and raised another fund and since have raised six funds, each one just about doubling in size from the one before, and we've made over 300 investments in early-stage technology companies and a lot of them are direct-to-consumer commerce, and so I got obsessed with direct-to-consumer commerce.

When I was running Thrillist, I said, "How do we take these direct-to-consumer-commerce companies that we're investing in and some of that philosophy and marry that with what we're building at Thrillist?" JackThreads was a company which was an advertiser at Thrillist, and a successful advertiser — they spent money with us and people signed up, spent money with them, and we said "right time, right place, right value," and we decided to buy JackThreads six years ago at Thrillist to get into content and commerce.

Selling versus spinning out, an emotionally draining experience

Shontell: So you buy this company and it does boost your revenue a bunch, but then eventually you end up spinning it out. What happened?

Lerer: We brought it in and we started growing two businesses at once: a media business and a commerce business. And as is sometimes the case, the new thing that comes in is the shiny object, and so we start putting a lot of focus into integrating it in, into investing it and growing it, and JackThreads explodes and starts growing super quickly. And you turn back and look at your media business a year later and go, "Ah, that hasn't grown because we haven't put any time into it and we haven't invested money into it and we sort of took for granted that it was going to continue to grow."

You then go back and go, "OK, we've got to get this media business back on track, and then you turn back and look at your retail business six months later and go, 'That's not growing as fast as it was.'" So then we get to this point and go, "OK, guys, we need to divide and conquer, and we need to start growing our management team, we need to put more resources against this." We went out and raised a Series A from Oak, from Fred Harmon at Oak, and that was to fund growth in both business and Fred came in.

Shontell: And he's been an investor in a lot of media companies — Bleacher Report, a bunch.

Lerer: Bleacher, HuffPo, NowThis, Brit and Co. Fred gets it, and we built a great relationship with Fred. A lot of investors loved the idea, but it was harder to raise money than it should have been. We were like, "Eh, look, it is what it is, let's just put our heads down and grow these two businesses" and a few things happened.

One is, each of them started changing, and so Thrillist started becoming more gender-neutral as the audience got bigger, and JackThreads got into the business of making its own stuff, and both businesses as we were investing started requiring more capital, and they need different kinds of capital, and they need different kinds of talent, and so then we built separate management teams and the businesses, which at one point were in the same boat, or in boats sitting beside each other going the same direction, started diverging.

And so you know, whatever it was, two and a half years ago, I think, when we ended up closing the financing, Axel Springer came in and invested and as part of their investment, they basically said, "Look, we love your media business, and we want to grow your media business." As you would know, they are fans of the media business and are now the owners of BI. And actually this was within the same month that they bought BI.

Shontell: This is about two years ago.

Lerer: Two years ago, OK. That's when we closed. I think we looked at Thrillist and said, "A lot has happened in the media business and the rise of social and the opportunity that we saw around the corner with video — which is now the very foundation of what Group Nine is all about — we said there's this bigger, more exciting thing happening and we don't want to be half in, half out, and we want to go and grow media. We said, "Let's spin JackThreads and put it in a separate thing. It'll become an LHV investment and we'll bring in new money and a new CEO and it'll have its own course and it will be a separate thing from us."

So we did that and put our head down on Thrillist and just focused and grew like a weed, and it was like that reminder of, we're good at this business, if we pay attention and if we don't lose sight of the fundamentals of what we're trying to build. And so we grew Thrillist really nicely, and then all the while had this idea that there were changes happening in media that were big and exciting.

That time Thrillist almost got bought by Axel Springer or Viacom

Shontell: Some would look at the big and exciting changes in media and actually be a little bit scared because it means a lot more investment, a whole change in business model to some extent as different medias keep forming. So some would look at that and be, like, "OK, this is time to get out. I've built a great thing, I've built a great brand, I've done this for eight years or whatever it had been at that point. I'm done."

Did you think that? Like, I know that there had been rumors of acquisition talk along the years at Thrillist. What was the closest you ever came?

Lerer: The closest we ever came was when we did the spin of JackThreads, because that was emotionally hard. That was physically hard. You build the team, you build the culture, it's all your people and we're, like, "This is going to be hard," and it was. And that was a moment where when we were splitting the two things. We got really close to selling it and we had multiple people who I think would have bought it and who we were having real conversations with.

Shontell: Like who?

Lerer: Like Axel. We spent a bunch of time with them. It was in the press that we spent a bunch of time with Viacom. By the way, I don't think that selling is in any way, shape, or form giving up or copping out or throwing in the towel — at all. I just thought that it wasn't really the right time for us, and this again comes back to my dad.

At that time, he said something to me that was really important, that was a big driving factor, where he said, "Look at what's happening in media, look at the changes that are going on. This feels like the cable-TV business to me in the '80s, where you have these strong brands that people care about with big growing audiences on the new distribution platforms on social, and it's like the Wild West, and the money's not all there yet but the audiences are huge and, boy, history's repeating itself."

He said, "I see something happening. I remember being almost your exact age, in 1982, and seeing consolidations start to come to cable, and I didn't have a front-row seat. You have your buy-in. You have a chip to play a real role here in Thrillist. You own one of the 20 or 30 or 40 brands that matter in digital, and if I were in your shoes, I would think about taking what you have and doubling down. So you don't build a brand in the wind to get bought, but you build the next holding company."

And we thought about that idea and it sounded really compelling. I literally just looked at everything happening in digital media and I said, "If I started Thrillist again today, how would I built it? What would it look like?" You build totally around your consumer, you unapologetically go to where they are, you unapologetically create in the format that is going to get the most distribution. Go to where the people are and build giant brands that tons of people love and like money always does follow these things.

Creating Group Nine and becoming king

Discovery and CEO David Zaslav went all in investing about $100 million in Group Nine. Alberto E. Rodriguez/Getty Images for Discovery Communications

Shontell: So you now run Group Nine, which ended up kind of consolidating all these things into one.

Lerer: The Dodo, NowThis.

Shontell: All these very different companies.

Lerer: And Thrillist.

Shontell: They were all media. How did that discussion happen? How did you decide, "OK, we're going to take NowThis, The Dodo, have them all agree to join," and then come up with this structure where you're suddenly king?

Lerer: Rude! So the structure was — I mean, this is not like deal making for the faint of heart.

I definitively remember this: It was a year ago, it was during the summer because I remember where I was running. I was running outside and I was having a call with Fred and I was telling him about this idea and he said, basically, "Don't quit your day job." Like, "Good luck putting these things together. It's a really great idea, but these companies have different boards with different investors, with different priorities. They have different management teams."

There was a lot of crossover investors, so Axel was in Thrillist and Axel was in NowThis. Greycroft may have been in two out of three, LHV was in all three, Fred Harmon, I believe, was in all three of them. The only outside investor of scale at any of the companies, other than Axel and Fred and Lerer, was Discovery, who was a big investor at The Dodo. It took a lot of spending time with the management teams of the other businesses to all have a meeting of the mind on how this would look and what the structure would be, and we were right about a bunch and wrong about a bunch, and we continue to learn as we put the businesses together.

The philosophy was, if we're going to build the biggest digital holding company for a bunch of reasons, it would make sense to be partnered with one of the biggest traditional holding companies. And so because Discovery had had a very positive experience with the Dodo, and because we thought that it just aligned with us for a bunch of reasons, they were one of a very small handful of folks that we sort of teased this idea to, which we called Project Family. It was our secret name, and Discovery was decisive and aggressive and ambitious and self-aware, and they said, "This is hard and we're doing this here. Let's be all in with you guys while we make a big investment, let's also contribute our digital footprint, and we're not going to try to compete with you. You guys will build digital and we're going to do what we do great and we'll find ways to partner in a thousand different ways, but Seeker will be part of the Group Nine family and so Seeker is our fourth brand."

Shontell: So you're creating content for platforms like Facebook and Instagram and Snapchat and you're pumping it out to them and you're letting them be the distribution. Do you guys even need websites or are you just doing distributed?

Lerer: We have websites. I think a website is there because of search and because if you're building brands that answer questions that people might have, you should be there for those people. I think you build them for hyper fan bases. We'll have tens and tens of millions of uniques across our properties because we have brands that matter.

Shontell: Those are people coming to your websites to check it out.

Lerer: Yeah, and we'll have big audiences there. That is an output of having brands that matter. That's not the business.

Shontell: So you're the head now of four different brands?

Lerer: Well, each brand has its own leads. So I'm not the head of the brands; I'm the head of the holding company that owns the brands. But the brands operate totally independently from an editorial perspective. Lots of shared learning, shared insights, shared technology, shared go-to-market from an advertising perspective. Like, we're consolidating at the sort of Group Nine level as much as we can to get best practices and learning and efficiency but the brands themselves are wholly independent editorial operations with their own mission, their own soul, their own direction.

Shontell: And you said that Discover went all in, they invested about $100 million into this new digital entity, holding company, and I think you were valued at $580 million through this deal.

Lerer: I think we want to build the best content brands and the best IP creation brands for the next generation of consumers, and part of the philosophy of creating great content is creating content with the user at the center, meaning, we're going to make it for where people are, not for where we can capture them or trap them.

Shontell: Right: where it's convenient for them. One thing that it seems like you guys and a lot of other folks are really doubling down — and this probably comes into play when you talk about disrupting cable and cable coming together with print and all that — is video. Video is taking over; social video is everywhere.

Are you all video content now? Is that where you're heading? Is text dead? What's happening?

Lerer: We're not all video content. Text is not dead.

We want to first think how a story is told in sight, sound, and motion, but with a lot of stories, that's not the best way to consume, that's not the best way to distribute. And so the idea is we're building brands, brands that stand for something, they're going to create a wide array of content. Most of it, probably, is going to be video, but that is not to say at all that like we don't believe in non-video content, and Thrillist is a perfect example. We're winning James Beard Awards for our journalism and our feature writing, and telling really interesting and important stories. Huge numbers of people are relying on us to come and read about local food and drink, and that's part of being a brand that does everything that your audience could want you to do, but we're a video company.

You know, Facebook is not a social network; Facebook is a mobile-video-distribution platform. All these platforms are trying to build the mobile version of television, and there's a really good reason for it because there's upwards of $70 billion in the US TV market that they would all like to have, and so we're building on the backs of the pipes, and the pipes want video because people want video, and because the business is in video, and so we're building the future of TV networks — and that's video.

What he says to people who say success breeds success

The apple doesn't fall far from the tree for Ben and Ken Lerer. GettyImages

Shontell: So a couple of personal questions to wrap this all up. Don't worry — not too personal.

Lerer: Oh, my God.

Shontell: We've talked a lot about where you came from and your dad and how he's been a big influence on your life, and I would say that one of the biggest criticisms that people who are successful who have successful parents get is "success breeds success, and you are successful because you came from privilege."

So I don't think that you would have stuck it out and gone through all this pain of building a 10-year-plus media company if that were the only thing driving you, but how do you respond to that? When people have that criticism, what do you say?

Lerer: What I would say is like, yeah, I totally get that, and who am I kidding? I just told you the story of my career, and arguably the two most important decisions I've made were in some way, shape, or form taking my father's advice, so I'm hardly shying away from the idea that my dad has been incredibly helpful to me. His success is not what has been helpful for me; he actually helps me. He gives me the best advice ever. So what can I say? I mean, yeah — he's been helpful.

Shontell: But can you be successful without it? Like, not you personally, but in general.

Lerer: Well, of course you can be successful without it.

Shontell: Can you build a big company?

Lerer: Of course you can, and people do that all the time.

I've had the benefit of having him help me, and it's been helpful, and I believe I'm more successful because of the help I've gotten from him, so I'm not going to shy from away from it and be, like, "I would do it all without my dad." My dad has not given me money for my companies, but he's been helpful, and, by the way, where's the line between nepotism and the apple doesn't fall far from the tree? I think that there are people who know my dad, who think my dad's smart, who maybe give me an extra look because they're, like, "Hey, maybe this guy comes from OK genes," and my sister has been pretty successful, like, clearly something OK is going on. We're not morons. I will lean right into, like, "My dad has helped my career and I appreciate it, and I'm happy to acknowledge it."

Shontell: Well, you should never apologize for where you came from, and I think it's a huge testament to you that you've been so ambitious and built such a great career for yourself regardless.

Lerer: That is so sweet of you.

Shontell: Where does that ambition come from? You could have just sat back and been like a sloppy college kid forever, but you're not that person and you built this huge media company that you want to become even bigger, so you're working your butt off. What drives you and how did you get that ambition?

Lerer: One, insecurity, the great motivator.

Shontell: I think when you have successful parents, too, you want to prove that you can do it yourself.

Lerer: You know what's funny, I agree with that. At the same time, I grew up in Manhattan and went to Dalton, and many of my friends had super-successful-whatever parents, and it didn't turn out to be the great motivator for all of them. For me it's fear of failure, first and foremost — that's a huge driver. I wish that wasn't the case, but it is, and then a lot of it is just the meaning of life. What is your life and how do you make the most of it?

There are so many times where this is hard and I'm like, "Oh man, I could live an easier life," but it's not actually appealing. Why get out of bed in the morning? You've got to do stuff and make stuff, and particularly I think Group Nine is really mission-driven. There's been nothing that has been a greater pleasure for me than with this political environment and this disgusting president to have NowThis news be part of our portfolio and to see the change that they're making and the people that they're giving voices to. That's amazing, and I'm really proud of the work that they're doing and feel lucky to be a part of it, and that's an example of, like — that's being alive.

Shontell: Great. Well, thank you so much, Ben. It's been fun.

Lerer: Thank you. Thanks for having me.

Disclosure: Ken Lerer is an investor in Business Insider through Lerer Ventures.